The occupancy rate for short-term rentals in Des Moines, Iowa varies throughout the year mainly due to the seasonality of the Iowa weather. 

We average around 80-120 gallons per day and with the warmer weather finally arriving I suspect it will be higher.

You should also be mindful of your local neighborhoods Zoning laws (check NYC Zola website) before forecasting anything out and starting work. 

It's good to be a little nervous, that means you are learning and growing, and it keeps you in check, so you don't get out over your skis, it's actually good to listen to your body, I'm not saying don't take action, but I'm saying maybe run a stress test on your liquidity to make sure you can weather any storm, I have founding that adding cash to my reserves always helps me sleep better at night.

The weather down there is great and a lot of people are retiring to the area for that reason.

The boards are clearly weathered as all heck, and I'd want to improve the look and wear. 

Strictly from a roofing system, weather protection standpoint, a pitched roof is much less likely to encounter leak issues, unless it is damaged by outside forces (think hail, high wind, tree limbs, etc.).  

@Rosa Weatherly Did you figure out a good company to go with?

Mostly good weather.

No place else in the USA to get mountains, ocean, and year-round great weather.